Ethyl Acetate → HCID 131718451, compound

HRID 1109114Notes

Reaction equation

HRID 1109114 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:13][CH2:14][CH2:15][N:16]2[C@@H:24]3[C@@H:19]([C:20]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:21]=4[CH2:22][CH2:23]3)[CH2:18][C:17]2=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(OCC)(=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:7]1([CH2:13][CH2:14][CH2:15][N:16]2[C@@H:24]3[C@@H:19]([C:20]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:21]=4[CH2:22][CH2:23]3)[CH2:18][CH2:17]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 131718450HCID 131718450, compound

Product 1

HCID 131718451HCID 131718451, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.38 g (0.010 mol) of lithium aluminum hydride was suspended in 40 ml of THF under argon. A solution of 3.26 g (0.00955 mol) of rac-cis-3-(3-cyclohexyl-propyl)-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one in 30 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 2 hours. Then, 10 ml of ethyl acetate and a saturated aqueous Na2SO4 solution were cautiously added dropwise thereto in succession until a complete white precipitate had resulted. After filtration and concentration there was obtained an oil which was chromatographed over silica gel with cyclohexane/ethyl acetate 1:1. There were obtained 2.64 g (84%) of oily rac-cis-3-(3-cyclohexyl-propyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

Workup

  1. temperatureunder reflux for 2 hours
  2. customin succession until a complete white precipitate had resulted
  3. filtrationAfter filtration
  4. concentrationconcentration there
  5. customwas obtained an oil which
  6. customwas chromatographed over silica gel with cyclohexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-301d92da5809478aa1649ea8fa398883
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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